Reaction product of hydrazine and its derivatives with diazophenol and its derivatives, and salts of such products



' o I United States Patent ce 1 i 1 Patented Dec. 27-, 1955 omNmNm) 2, 28,760 I REACTIoN PRODUCT BEHYDRAZINE AND. ITS WITH DIAZOPHENOL AND ITS 5 I DERIVATIVES, AND SALTS- OF SUCH PRODUCTS ioseph F-(Kenney, Milford, Conm, assignor to Remington N Arms Company; Inc., Bridgeport, C'onn., a corporation 0K of Delaware k NoDr-awing. Application December 9, 1952, OIN N==N-H-N-Hz+ (NHiNHWHNOi Serial No. 325,042

6'Claims; (Cl. 260--I40) N01 Thlslnvention relates to aclass or group of compounds U Numerous other salts of 2Y,4 dinitm 6- (tetmzem4 v whlqh are lqemlfi-gd .ggneriaily profiucts h reactvlim phenol have been prepared and their explosive properties of f and P YS h F- and determined on a temperature gradient bar as follows: derivatives, and thesalts of such. reaction products. 7 V v These compounds are characterizedabya tetrazened linkg age I i Explosion Points l I in5se 1112s nlia 1 C. S 0. 8Il8- N N N N t ,atpea antjoining a phenolic ring. Their characteristic structure is: ca 0C1; c

196 200 205 193 195 20s 011x 212 215 217 180 182 192 158 162 166 -N=NX 160 162 165 200 205 209 160 163 167 192 196 200 Preparation of the hydrazine salt of 2,4-dinitr0-6- tetrazeno-I -phenol 15 grams of diazodinitrophenol are suspended in 100 cc. of alcohol and 100 cc. of water. 10 cc. of hydrazine hydrate is dissolved in 50 cc. of water, and the hydrazine solution is added to the diazodinitrophenol suspension with stirring, which is continued for about minutes. The reaction appears to be O H (N HzNHs) This reaction product, which precipitates in red-brown needles, is the hydrazine salt of 2,4-dinitro-6-(tetrazeno- 1)-pheno1.

Preparation of a potassium salt of 2,4-dinitro-6-( tetrazeno-l -phenol To a suspension of 5 grams of the Washed and dried product of Reaction I above in cc. of water, there is added with stirring a solution of 10 grams of potassium nitrate in 50 cc. of water, the stirring being continued for 20 minutes. A dark red crystalline precipitate resulted from the reaction.

The salts of the reaction product of diazodinitrophenol and derivatives of hydrazine likewise have explosive properties. For example, the potassium, lead and silver salts of acetohydrazide, methyl hydrazine, and acetone hydrazone have been prepared and found very explosive. The invention contemplates the use, among others, of hydrazine derivatives of the types in which R, R and R" are any atom or group of atoms capable of the indicated combinations.

Typical of such hydrazine derivatives are:

H HN-N=O (0 Ba) 2 Acetone hydrazone The explosive properties of the novel compounds above set forth are such that they are particularly adapted for use as the explosive or;v sensitizing ingredient of atnmunition priming compositions, replacing wholly or in part such explosives astetrazene and its salts, normal or'b asic' Lead 2, 4-dinitro-6-(tetrazeno-1)-pheno1. Potassium 2, 4-dinitr0-6-(tetrazeuo-l)-phen0 40 Lead Styphnate 32 Potassium Nitrate. 27 Lead Nitrate 25 Glass 33 33 In the usual sensitivity (2 ounce weight) and powder ignition tests, the above compositions and a commercial Diazodinitrophenol is typical of many derivatives of diazophenol which, like diazophenol itself, combine with hydrazine and its derivatives to form compounds which, either as themselves or as metallic salts, have useful properties. For example, the lead salt of the reaction product of diazomononitrophenol and hydrazine explodes in 5 seconds at C. and instantaneously at C. The salts of the reaction product of diazophenol with hydra zine, likewise, have explosive properties. Other examples of derivatives of diazophenol usable in accordance with the presentinvention are 2,4 dichloro diazophenol; v3 amino diazophenol; and 2 methyl diazophenols What is claimed is:

. The compound 2,4-dinitro-6-(tetrazeno-1)-phenol. A metallic salt of the compound of claim 1. The lead salt of the compound of claim 1. The copper salt of the ,compound of claim 1. The cadmium salt of the compound of claim 1. The potassium salt of the compound of claim; 1.

References Cited in the file of this patent UNITED STATES PATENTS Rathsburg Oct. 14, 1924 Burns June 7, 1932 

1. THE COMPOUND 2,4-DINITRO-6-(TETRAZENO-1)-PHENOL. 